Transition metal catalyst-free, base-promoted 1,2-additions of polyfluorophenylboronates to aldehydes and ketones
Please always quote using this URN: urn:nbn:de:bvb:20-opus-256487
- A novel protocol for the transition metal-free 1,2-addition of polyfluoroaryl boronate esters to aldehydes and ketones is reported, which provides secondary alcohols, tertiary alcohols, and ketones. Control experiments and DFT calculations indicate that both the ortho-F substituents on the polyfluorophenyl boronates and the counterion K\(^+\) in the carbonate base are critical. The distinguishing features of this procedure include the employment of commercially available starting materials and the broad scope of the reaction with a wide varietyA novel protocol for the transition metal-free 1,2-addition of polyfluoroaryl boronate esters to aldehydes and ketones is reported, which provides secondary alcohols, tertiary alcohols, and ketones. Control experiments and DFT calculations indicate that both the ortho-F substituents on the polyfluorophenyl boronates and the counterion K\(^+\) in the carbonate base are critical. The distinguishing features of this procedure include the employment of commercially available starting materials and the broad scope of the reaction with a wide variety of carbonyl compounds giving moderate to excellent yields. Intriguing structural features involving O−H⋅⋅⋅O and O−H⋅⋅⋅N hydrogen bonding, as well as arene-perfluoroarene interactions, in this series of racemic polyfluoroaryl carbinols have also been addressed.…
Author: | Zhiqiang LiuORCiD, Goutam Kumar KoleORCiD, Yudha P. BudimanORCiD, Ya-Ming TianORCiD, Alexandra FriedrichORCiD, Xiaoling LuoORCiD, Stephen A. WestcottORCiD, Udo RadiusORCiD, Todd B. MarderORCiD |
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URN: | urn:nbn:de:bvb:20-opus-256487 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Language: | English |
Parent Title (English): | Angewandte Chemie International Edition |
Year of Completion: | 2021 |
Volume: | 60 |
Issue: | 30 |
Pagenumber: | 16529–16538 |
Source: | Angewandte Chemie International Edition (2021) 60:30, 16529–16538. DOI: 10.1002/anie.202103686 |
DOI: | https://doi.org/10.1002/anie.202103686 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie |
Tag: | 1,2-additionreaction; alcohol; boronateesters; fluoroarene; inorganic chemistry; transition metal-free |
Release Date: | 2022/02/22 |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |